JPH0711290A - Cleaning composition - Google Patents

Abstract

PURPOSE:To obtain the subject composition useful for cleaning clothes, skin, hair, etc., having excellent hard water resistance and dispersibility, highly preventing effect on recontamination, extremely low irritation to skin, containing an alpha-sulfo fatty acid derivative having a specific structure. CONSTITUTION:The objective composition comprises preferably 5-40wt.% of an alpha-sulfo fatty acid derivative of formula I (R1 and R2 are 6-18C alkyl or alkenyl; R3 is H, l-6C alkyl, etc.; M1 and M2 are H, alkali metal, etc.; Z is 2-6C straight-chain or branched chain alkylene or 3-8C alkylene containing hydroxyl group as substituent group) (e.g. Na salt of monoethanolamine bis alpha-sulfopalmitic acid amide ester) as a cleaning agent component. The compound of formula I, for example, is obtained by a method of treating a compound of formula II with thionyl chloride, amidating the prepared acid halide with an amino-alcohol of the formula HR3N(Z)OH, esterifying the prepared compound of formula III with an A-sulfo fatty acid of formula IV and optionally neutralizing.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to clothes, hard surfaces, woody surfaces, leather surfaces, hair or skin which are excellent in hard water resistance and dispersibility, have a high anti-soil redeposition effect, and have extremely low skin irritation. It relates to a detergent composition suitable for use.

[0002]

2. Description of the Related Art The presence of a surfactant is indispensable for cleaning various stains, and a great number of detergent compositions having good detergency based on its ability to reduce interfacial tension and wettability have been proposed. There is. However, in order to obtain an excellent cleaning performance in the true sense, not only can the dirt be removed by the above-mentioned surface-active ability, but also the dirt can be easily removed in hard water. It must also be taken into consideration that it is dispersed in the surface and does not adhere to the surface again, that is, it prevents recontamination due to its excellent hard water resistance and dispersibility. The conventional detergent compositions are not necessarily those having sufficient hard water resistance, dispersibility and anti-soil redeposition property, and are not detergent compositions having really good cleaning performance. Further, the skin irritation of the cleaning agent is also a serious problem. Since there is a sufficient possibility that the detergent will come into contact with the skin in any washing, it is desired that the detergent has extremely low irritation to the skin.

[0003]

DISCLOSURE OF THE INVENTION The present invention relates to hard water resistance,
An object of the present invention is to provide a detergent composition which is excellent in dispersibility, has a high anti-soil redeposition effect, and has extremely low irritation to the skin, and is effective for washing clothes, hard surfaces, wood surfaces, leather surfaces, skin or hair. To do.

[0004]

According to the present invention, there is provided a detergent composition containing an α-sulfofatty acid derivative represented by the following general formula (1):

[Chemical 1] {In the formula, R₁, R₂: An alkyl group having 6 to 18 carbon atoms or
Lucenyl group R₃ : Hydrogen, an alkyl group having 1 to 6 carbon atoms or hydro
Xyalkyl group M₁, M₂: Hydrogen atom, alkali metal, monovalent
Lucari earth metal, substituted or unsubstituted ammonium group Z: a linear or branched chain alkyl group having 2 to 6 carbon atoms
C3 having a alkylene group or a hydroxyl group as a substituent
A linear, branched or cyclic alkylene group of
Represent. ) Especially for washing clothes, or for hard surfaces,
Use for wood surface, leather surface, skin or hair
The cleaning composition is provided, which is characterized by

That is, the inventors of the present invention have conducted extensive studies to solve the above-mentioned problems, and as a result, the detergent composition contains the specific α-sulfofatty acid derivative represented by the general formula (I). By doing so, it was found that the above object can be achieved, and the present invention has been completed.

The present invention will be described in more detail below. R ₁ and R ₂ in the general formula (1) are alkyl groups or alkenyl groups having 6 to 18 carbon atoms, and more preferably alkyl groups or alkenyl groups having 10 to 16 carbon atoms. The alkyl group or alkenyl group may be linear or branched. Specific examples of R ₁ and R ₂ include, but are not limited to, a decyl group, a dodecyl group, a tetradecyl group, and a hexadecyl group. R ₃ in the general formula (1) is hydrogen or an alkyl group having 1 to 6 carbon atoms or a hydroxyalkyl group, more preferably hydrogen, a methyl group, an ethyl group or an ethanol group.

M ₁ and M ₂ in the general formula (I) are a hydrogen atom, an alkali metal, a monovalent alkaline earth metal,
Alternatively, it is a substituted or unsubstituted ammonium group. Here, the alkaline earth metal corresponding to monovalent is, for example, M ₁
And M ₂ are one alkaline earth metal and form a salt. Specific examples include alkali metals such as sodium and potassium, examples of alkaline earth metals include magnesium and calcium, and further examples of substituted or unsubstituted ammonium groups include ammonia-derived ammonium groups. Examples include, but are not limited to, substituted amines formed from amines of lower amines (trimethylamine, triethylamine, etc.), lysine, mono-, di-, or tri-lower alkanolamines (monoethanolamine, diethanolamine, triethanolamine, etc.). Not a thing.

Z in the general formula (1) has 2 carbon atoms.
Is a linear or branched alkylene group having 6 to 6 carbon atoms, or a linear, branched or cyclic alkylene group having 3 to 8 carbon atoms and having a hydroxyl group as a substituent. Specific examples of Z include the following amino alcohol residues. Monoethanolamine, diethanolamine, isopropanolamine, ethylmonoethanolamine,
Butylmonoethanolamine, N-methylglucamine,
Glucamine etc.

The α-sulfofatty acid derivative represented by the general formula (I) can be produced, for example, by a method according to the reaction formula shown in Table 1 below. The sulfonated compound (2) obtained by sulfonating a fatty acid is treated with thionyl chloride to obtain a corresponding acid halide (3), which is then amidated with a predetermined amino alcohol to obtain an amidated compound (4). Further, a method of esterifying the amidation product (4) with α-sulfofatty acid and neutralizing it as necessary [Method A] or a sulfonation product (5) or (6) of a fatty acid or a fatty acid alkyl ester with a predetermined amino alcohol. It is obtained by amide esterification with [Method B].

[0010]

[Table 1] The amide esterified product obtained by the above method can be obtained as a mixture containing amide and the like, and the target amide ester can be separated by an appropriate purification means.

The α-sulfofatty acid derivative of the present invention is used as a detergent component. In this case, the concentration in the detergent may be any concentration as long as a cleaning effect can be obtained. Usually, it is preferably 1 to 50% by weight, more preferably 5 to 40% by weight.

Further, in the cleaning agent of the present invention, a component which is usually used as a cleaning agent component according to various cleaning purposes can be optionally used in combination within a range not impairing the effects of the present invention. For example, zeolite, sodium carbonate (potassium), sodium silicate, sodium citrate, builder such as polyacrylate, moisturizer such as (poly) glycerin, sorbitol, (poly) ethylene glycol,
(Poly) propylene glycol, methyl cellulose, polyoxyethylene glycol distearate, viscosity modifiers such as ethanol, preservatives such as methylparaben and butylparaben, anti-inflammatory agents such as potassium glycyrrhizinate and tocopherol acetate, other bactericides, pearls Agents, antioxidants, fragrances, dyes, ultraviolet absorbers and the like can be added as necessary.

Further, the detergent of the present invention may be used in combination with other surfactants. Examples of such a surfactant include alkylbenzene sulfonate and α
-Olefin sulfonate, α-sulfo fatty acid alkyl ester salt, alkyl sulfate ester salt, polyoxyethylene alkyl sulfate ester salt, sulfosuccinic acid mono (di) alkyl (alkenyl) ester-based surfactant,
Alkyl phosphate ester-based surfactants, amino acid-based surfactants, taurate-based surfactants, anionic surfactants such as higher fatty acid salts, alkyl saccharide-based surfactants, polyoxyethylene alkyl ether-based surfactants, etc. Nonionic surfactants and the like are preferably used.

The detergent composition of the present invention is excellent in hard water resistance and dispersibility, and exhibits a high anti-soil redeposition effect during washing. The detergent composition is effective as a detergent composition for various products including clothes, and since the composition of the present invention has extremely low skin irritation, contact with at least a part of the human body is particularly important. The application is preferably applied as a cleaning composition for hard surfaces, wood surfaces, leather surfaces, skin and hair. In this case, examples of the hard surface include metal surfaces such as tableware and automobile bodies, plastic surfaces, and ceramic surfaces. Furniture and pillar surfaces are examples of wood surfaces. Examples of the leather surface include surfaces of handbags and boots. Therefore, the cleaning composition of the present invention is a cleaning agent for use in contact with a human body, for example, a liquid cleaning agent for skin hair such as body shampoo and shampoo, a liquid cleaning agent for tableware, and a wall or floor for residential use. It is suitable as a liquid cleaning agent. Further, the cleaning composition of the present invention can be used in the form of solid, powder, paste or liquid depending on the application.

[0015]

The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples.

Examples 1 and Comparative Examples 1 and 2 The detergent compositions containing the respective surfactants A to E shown in Table 2 below were evaluated for skin irritation, dispersibility and hard water resistance by the methods described below. did. (Skin irritation) An upper arm closed patch test was conducted on 20 samples for 5 days using a 5% by weight aqueous solution of a surfactant as a test solution. The evaluation method is as follows. <Evaluation method> ○: Cases of red discoloration, rash, etc. = 0 cases △: Cases of occurrence = 1 ×: Cases of occurrence = 2 or more (Dispersibility) 0.01% by weight of carbon black and 0.1
50 ml of a sample aqueous solution containing a surfactant by weight was prepared and shaken in a constant temperature bath at 25 ° C. for 5 hours. Then 24
After allowing to stand for a time, the dispersion state was evaluated according to the following method. <Evaluation method> Good: Carbon black is uniformly dispersed. X: There is a separation layer. (Hard water resistance) 40 ml of 0.5 wt% aqueous surfactant solution
Was placed in a 100 ml beaker, 8.5 ml of a 1 wt% calcium acetate aqueous solution was added dropwise, and the hard water resistance was evaluated according to the following method. <Evaluation method> ○: The type letters pasted on the bottom of the beaker are visible. X: The type letters pasted on the bottom of the beaker cannot be seen.

[0017]

[Table 4] A: Monoethanolamine bis α-sulfopalmitic acid amide Na salt B: Diethanolamine bis α-sulfostearic acid amide Na salt C: Isopropanolamine bis α-sulfomyristic acid amide Na salt D: Glucamine bis α-sulfopalmitic acid Amide ester Na salt E: N-methylglucamine bis α-sulfomyristate amide ester Na salt F: Dodecyl sulfate Na salt G: Coconut oil fatty acid soap Na salt

[0018] Example 2 [clothing detergent (granular detergent)] (component) (wt%) monoethanolamine bis α- sulfo C ₁₄ ~ ₁₆ fatty amide ester Na salt 15.0% alkylbenzene sulfonic acid K salt 10. 0% Alcohol ethoxylate 5.0% Zeolite 20.0% Potassium carbonate 5.0% Sodium carbonate 20.0% Sodium sulfate 18.5% Enzyme 0.5% Moisture 6.0% Granular detergent for clothes with the above composition Was manufactured. This granular cleaning agent for clothes had an excellent anti-redeposition ability, and a good cleaning effect was obtained.

[0019] Example 3 [clothing detergent (granular detergent)] (component) (wt%) diethanolamine bis alpha-sulfo C ₁₆ ~ ₁₈ fatty amide ester Na salt 13.0% alpha-sulfo C ₁₄ ~ ₁₈ fatty acid methyl ester Na salt 7.0% C ₁₄ ~ ₁₈ α- olefin sulfonate K salt 13.0% alcohol ethoxylate 4.0% zeolite 20.0% sodium 8.0% sodium carbonate potassium carbonate 6.0% silicate 9 0.0% Sodium sulfate 23.5% Enzyme 0.5% Moisture 6.0% A granular detergent for clothes having the above composition was produced. This granular cleaning agent for clothes had an excellent anti-redeposition ability, and a good cleaning effect was obtained.

Example 4 [Kitchen cleaner] (Component) (wt%) Monoethanolamine bis α-sulfomyristate amide ester Na salt 13.0% Polyoxyethylene (EOp = 3) alkyl sulfate ester Na salt 5 0.0% Coconut oil fatty acid diethanolamide 3.0% Dodecyldimethylamine oxide 2.5% Ethanol 4.0% Yellow No. 203 Trace fragrance Trace ion exchanged water balance A kitchen cleaner (PH 7.0) having the above composition was produced. . This cleaning agent for kitchen was excellent in anti-soil redeposition ability, and there was no stain remaining on the dishes, and a good cleaning effect was obtained. In addition, this kitchen cleaning agent did not give a feeling of rough hands after use.

Example 5 [Kitchen cleaner] (Component) (wt%) N-methylglucamine bis α-sulfomyristate amide ester Na salt 10.0% Polyoxyethylene (EOp: 3) alkyl sulfate ester Na Salt 3.0% Coconut oil fatty acid diethanolamide 5.0% Ethanol 4.0% Yellow No. 203 Trace fragrance Trace ion exchanged water balance A kitchen cleaning material (pH 7.0) having the above composition was produced. This cleaning agent for kitchen was excellent in anti-soil redeposition ability, and there was no stain remaining on the dishes, and a good cleaning effect was obtained. In addition, this kitchen cleaning agent did not give a feeling of rough hands after use.

Example 6 [Shampoo] (Component) (% by weight) Diethanolamine bis α-sulfomyristate amide ester Na salt 12.0% Palm oil fatty acid amide propyl betaine 4.0% Palm oil fatty acid diethanolamide 3.0% β-carotene trace amount fragrance amount trace amount ion-exchanged water balance A shampoo (pH 6.5) having the above composition was produced. This shampoo had an excellent anti-soil redeposition ability, a high cleaning effect, no squeaky feeling during use, and good wash-out.

Example 7 [Shampoo] (Component) (% by weight) Isopropanolamine bis α-sulfomyristate amide ester Na salt 8.0% Polyoxyethylene (EOp: 3) alkyl sulfate Na salt 7.0% Palm Oil fatty acid diethanolamide 4.0% Dodecylamine oxide 2.5% Perfume Trace ion-exchanged water balance A shampoo (pH 6.5) having the above composition was produced. This shampoo had an excellent anti-soil redeposition ability, a high cleaning effect, no squeaky feeling during use, and good wash-out.

Example 8 [Detergent for Household] (Component) (wt%) Monoethanolamine bis α-sulfopalmitic acid Na salt 5.0% Polyoxyethylene (9) dodecyl ether 2.5% Yellow No. 203 Trace amount Fragrance Trace amount Ion-exchanged water balance A household cleaning agent (pH 7.0) having the above composition was produced. This household cleaning agent has an excellent anti-redeposition ability and a good cleaning effect was obtained. In addition, this cleaning agent for homes did not make the hands feel rough even if it adhered to the hands.

[0025]

The detergent composition of the present invention has excellent hard water resistance and dispersibility, has an effect of preventing redeposition, and has extremely low skin irritation. Then, the detergent composition of the present invention is preferably used for clothing or for use in contact with at least a part of the human body, such as hard surface, wood surface, leather surface, skin, and hair. To be done.

Claims (3)

[Claims] 1. An α-sulfur represented by the following general formula (1):
Detergent composition characterized by containing a fatty acid derivative
Stuff. [Chemical 1] {In the formula, R₁, R₂: An alkyl group having 6 to 18 carbon atoms or
Lucenyl group R₃ : Hydrogen, an alkyl group having 1 to 6 carbon atoms or hydro
Xyalkyl group M₁, M₂: Hydrogen atom, alkali metal, monovalent
Lucari earth metal, substituted or unsubstituted ammonium group Z: a linear or branched chain alkyl group having 2 to 6 carbon atoms
C3 having a alkylene group or a hydroxyl group as a substituent
A linear, branched or cyclic alkylene group of
Represent. ) 2. The cleaning composition according to claim 1, which is used for cleaning clothes. 3. A hard surface, a wood surface, a leather surface,
The cleaning composition according to claim 1, which is used for skin or hair.